Rubrene

As an organic semiconductor, the major application of rubrene is in organic light-emitting diodes (OLEDs) and organic field-effect transistors, which are the core elements of flexible displays. Single-crystal transistors can be prepared using crystalline rubrene, which is grown in a modified zone furnace on a temperature gradient. This technique, known as physical vapor transport, was introduced in 1998.[1][2]

Rubrene holds the distinction of being the organic semiconductor with the highest carrier mobility, reaching 40 cm²/(V·s) for holes. This value was measured in OFETs prepared by peeling a thin layer of single-crystalline rubrene and transferring to a Si/SiO₂ substrate.[3]

Several polymorphs of rubrene are known. Crystals grown from vapor in vacuum can be monoclinic,[4] triclinic,[5] and orthorhombic motifs.[6] Orthorhombic crystals (space group B_bam) are obtained in a closed system in a two-zone furnace at ambient pressure.[7]

Rubrene is prepared by treating 1,1,3-Triphenyl-2-propyn-1-ol with thionyl chloride.[8]

The resulting chloroallene undergoes dimerization and dehydrochlorination to give rubrene.[9]

Rubrene, like other polycyclic aromatic molecules, undergoes redox reactions in solution. It oxidizes and reduces reversibly at 0.95 V and −1.37 V, respectively vs SCE. When the cation and anion are co-generated in an electrochemical cell, they can combine with annihilation of their charges, but producing an excited rubrene molecule that emits at 540 nm. This phenomenon is called electrochemiluminescence.[10]